5-Fluoro-L-tryptophan

Base Information

• Chemical Name: 5-Fluoro-L-tryptophan
• CAS No.: 16626-02-1
• Molecular Formula: C11H11FN2O2
• Molecular Weight: 222.219
• Hs Code.: 2933990090
• UNII: 17H03VO4KZ
• DSSTox Substance ID: DTXSID501020654
• Nikkaji Number: J232.144K
• Wikidata: Q27094256
• Metabolomics Workbench ID: 147841
• ChEMBL ID: CHEMBL559973
• Mol file: 16626-02-1.mol

Synonyms:5-fluoro-(beta-11C)tryptophan;5-fluoro-L-tryptophan;5-fluorotryptophan;5-fluorotryptophan, (DL)-isomer;5-fluorotryptophan, (L)-isomer;5-fluorotryptophan, 18F-labeled;5-fluorotryptophan, 18F-labeled, (L)-isomer;L-5-fluorotryptophan

Chemical Property of 5-Fluoro-L-tryptophan

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 238-239 °C
• Refractive Index: 1.643
• Boiling Point: 450.7 °C at 760 mmHg
• PKA: 2.21±0.10(Predicted)
• Flash Point: 226.4 °C
• PSA: 79.11000
• Density: 1.442 g/cm³
• LogP: 1.96170
• Storage Temp.: 2-8°C
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 222.08045576
• Heavy Atom Count: 16
• Complexity: 275

Purity/Quality:

98%,99%, ^*data from raw suppliers

5-Fluoro-L-tryptophan ≥98.0% (HPLC) ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C=C1F)C(=CN2)CC(C(=O)O)N
• Isomeric SMILES: C1=CC2=C(C=C1F)C(=CN2)C[C@@H](C(=O)O)N
• Uses: Exogenous 5-fluoro-Trp is incorporated into proteins in normal protein synthesis. Since 19F is a useful reporter group, this provides a method for studying enzyme mechanisms by NMR.

Technology Process of 5-Fluoro-L-tryptophan

There total 14 articles about 5-Fluoro-L-tryptophan which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

Nα-acetyl-5-fluoro-D,L-tryptophan (7303-54-0) → Nα-acetyl-5-fluoro-D-tryptophan (320581-74-6) + 5-fluoro-L-tryptophan (16626-02-1,343-91-9,97749-24-1)

Guidance literature:

With borate buffer; cobalt(II) chloride; at 37 ℃; for 48h; pH=8.0; Enzymatic reaction;

DOI:10.1016/j.tetlet.2008.02.120

Reference yield: 83.0%

5-fluoro-1H-indole (399-52-0) + L-serin (56-45-1,83245-15-2) → 5-fluoro-L-tryptophan (16626-02-1,343-91-9,97749-24-1)

Guidance literature:

With Escherichia coli/pSTB₇ tryptophan synthase; pyridoxal 5'-phosphate; at 37 ℃; for 72h; aq. phosphate buffer;

DOI:10.1016/j.bmcl.2008.07.053

Reference yield: 70.0%

5-fluoro-L-tryptophan ethyl ester (261177-58-6,154170-01-1) → 5-fluoro-L-tryptophan (16626-02-1,343-91-9,97749-24-1)

Guidance literature:

With sodium hydroxide; In ethanol; water; at 50 ℃; for 2h;

DOI:10.1021/jo001679s

upstream raw materials:

5-fluoro-L-tryptophan ethyl ester

4-fluoro-2-iodoaniline

4-fluoroaniline

(2R,5S)-3,6-diethoxy-2-isopropyl-5-[3-(trimethylsilyl)prop-2-ynyl]2,5-diydropyrazine

Downstream raw materials:

(S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(5-fluoro-1H-indol-3-yl)-propanoic acid

(S)-2-((tert-butoxycarbonyl)amino)-3-(5-fluoro-1H-indol-3-yl)propanoic acid

C₆₆H₇₈N₁₄O₂₆

C₆₇H₈₀N₁₄O₂₆

Refernces

• 1、 Petrovic, Dejan M.,Leenhouts, Kees,Van Roosmalen, Maarten L.,Broos, Jaap. "An expression system for the efficient incorporation of an expanded set of tryptophan analogues". . p. 1329 - 1336. Retrieved 2013.
• 2、 Buller, Andrew R.,Brinkmann-Chen, Sabine,Romney, David K.,Herger, Michael,Murciano-Calles, Javier,Arnold, Frances H.. "Directed evolution of the tryptophan synthase β-subunit for stand-alone function recapitulates allosteric activation". . p. 14599 - 14604. Retrieved 2015/12/05.
• 3、 De Marco, Rossella,Bedini, Andrea,Spampinato, Santi,Gentilucci, Luca. "Synthesis of tripeptides containing d-Trp substituted at the indole ring, assessment of opioid receptor binding and in vivo central antinociception". supporting information. p. 6861 - 6866. Retrieved 2014/10/15.